Intermolecular Regio‐ and Stereoselective Hetero‐[5+2] Cycloaddition of Oxidopyrylium Ylides and Cyclic Imines

• Published in: Angewandte Chemie International Edition Vol. 58; no. 3; pp. 887 - 891
• Main Authors: Zhao, Changgui, Glazier, Daniel A., Yang, Daoshan, Yin, Dan, Guzei, IIia A., Aristov, Michael M., Liu, Peng, Tang, Weiping
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 14.01.2019; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: [5+2] cycloaddition; azepanes; Chemistry; Chemistry, Multidisciplinary; Cycloaddition; heterocycles; Imines; Natural products; Nitrogen; oxidoprylium ylide; Physical Sciences; Science & Technology; Stereochemistry; Stereoselectivity; Substitution reactions; VINYL AZIRIDINES; azepanes; oxidoprylium ylide; imines; ALKYNES; [5+2] cycloaddition; heterocycles; RING; 3-ACYLOXY-1,4-ENYNES; CHIRALITY; ACCESS; INTRAMOLECULAR 5+2 CYCLOADDITION; ALKALOIDS

We have developed the first intermolecular hetero‐[5+2] cycloaddition reaction between oxidopyrylium ylides and cyclic imines with excellent control of regio‐ and stereoselectivity. Surprisingly, divergent stereochemistry was observed depending on the substitution pattern of the oxidopyrylium ylide....